JP2011032298A - Coloring curable resin composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a coloring curable resin composition capable of forming a coating film causing no development unevenness. <P>SOLUTION: This coloring curable resin composition comprises a colorant (A), a binder resin (B), a photosensitizer (C), a curing agent (D), a solvent (E), and triphenylphosphine (F). <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to a colored curable resin composition.

An image sensor used for a digital camera or a digital video has a color filter.
As a method for producing a color filter, a method for producing a color filter by using a colored photosensitive resin composition in which a pigment such as a pigment or a dye is contained in a photosensitive resin composition typified by a photoresist has been developed. It has been.
According to the manufacturing method described above, a color filter that is an aggregate of pixels that are colored in the three primary colors of light (red, green, and blue) with pigments such as pigments and dyes is formed.

  As a colored curable resin composition for forming such a coating film, for example, a colored curable resin composition comprising a colorant, a binder resin, a photosensitive agent, a curing agent, and a solvent is disclosed (patent) Reference 1).

Japanese Patent Laid-Open No. 2002-14220

  However, in the coating film formed using the colored curable resin composition containing the colorant, binder resin, photosensitizer, curing agent, and solvent, development unevenness sometimes occurred. An object of the present invention is to provide a colored curable resin composition capable of forming a coating film that does not cause development unevenness.

  As a result of studying to find a colored curable resin composition capable of solving the above-mentioned problems, the present inventors have found that a colorant (A), a binder resin (B), a photosensitive agent (C), a curing agent (D), and a solvent. The present inventors have found that a coating film that does not cause development unevenness can be formed by the colored curable resin composition containing (E) and triphenylphosphine (F), and have reached the present invention.

［式（１）中、Ｒ^１〜Ｒ^４は、それぞれ独立に、水素原子、−Ｒ^６又は炭素数６〜１０の芳香族炭化水素基を表す。該芳香族炭化水素基に含まれる水素原子は、ハロゲン原子、−Ｒ^６、−ＯＨ、−ＯＲ^６、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、ＳＯ_３Ｍ、−ＣＯ_２Ｈ、−ＣＯ_２Ｒ^６、−ＳＯ_３Ｒ^６、−ＳＯ_２ＮＨＲ^８又は−ＳＯ_２ＮＲ^８Ｒ^９で置換されていてもよい。
Ｒ^５は、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、ＳＯ_３Ｍ、−ＣＯ_２Ｈ、−ＣＯ_２Ｒ^６、−ＳＯ_３Ｒ^６、−ＳＯ_２ＮＨＲ^８又は−ＳＯ_２ＮＲ^８Ｒ^９を表す。
ｍは、０〜５の整数を表す。ｍが２以上の整数である場合、複数のＲ^５は、同一であっても異なっていてもよい。
Ｘは、ハロゲン原子を表す。
ａは、０又は１の整数を表す。
Ｒ^６は、炭素数１〜１０の飽和炭化水素基を表す。該飽和炭化水素基に含まれる水素原子は、ハロゲン原子で置換されていてもよい。該飽和炭化水素基に含まれるメチレン基は、酸素原子、カルボニル基又は−ＮＲ^７−で置換されていてもよい。
Ｒ^７は、炭素数１〜１０の飽和炭化水素基を表す。該飽和炭化水素基に含まれる水素原子は、ハロゲン原子で置換されていてもよい。該飽和炭化水素基に含まれるメチレン基は、酸素原子又はカルボニル基で置換されていてもよい。
Ｒ^８及びＲ^９は、それぞれ独立に、炭素数１〜１０の直鎖又は分岐のアルキル基、炭素数３〜３０のシクロアルキル基又は−Ｑを表す。あるいはＲ^８及びＲ^９は、互いに結合して炭素数１〜１０の複素環を形成していてもよい。
Ｑは、炭素数６〜１０の芳香族炭化水素基又は炭素数５〜１０の芳香族複素環基を表し、該芳香族炭化水素基及び芳香族複素環基に含まれる水素原子は、−ＯＨ、−Ｒ^６、−ＯＲ^６、−ＮＯ_２、−ＣＨ＝ＣＨ_２、−ＣＨ＝ＣＨＲ^６又はハロゲン原子で置換されていてもよい。
炭素数１〜１０の直鎖又は分岐のアルキル基及び炭素数３〜３０のシクロアルキル基に含まれる水素原子は、水酸基、ハロゲン原子、−Ｑ、−ＣＨ＝ＣＨ_２又は−ＣＨ＝ＣＨＲ^６で置換されていてもよい。炭素数１〜１０の直鎖又は分岐のアルキル基及び炭素数３〜３０のシクロアルキル基に含まれるメチレン基は、酸素原子、カルボニル基又は−ＮＲ^６−で置換されていてもよい。炭素数１〜１０の複素環に含まれる水素原子は、−Ｒ^６、−ＯＨ又は−Ｑで置換されていてもよい。
Ｍは、ナトリウム原子又はカリウム原子を表す。］
［３］トリフェニルホスフィン（Ｆ）の含有量が、着色硬化性樹脂組成物の固形分に対して、２〜７質量％である前記［１］又は［２］記載の着色硬化性樹脂組成物。
［４］溶剤（Ｅ）が、乳酸エチル、プロピレングリコールモノメチルエーテル及びジアセトンアルコールからなる群から選ばれる少なくとも２種の溶剤を含んでなる溶剤である前記［１］〜［３］のいずれか記載の着色硬化性樹脂組成物。
［５］感光剤（Ｃ）が、ナフトキノンジアジドスルホン酸エステルである前記［１］〜［４］のいずれか記載の着色硬化性樹脂組成物。
［６］硬化剤（Ｄ）が、式（２）で表される２価の基を２つ以上有する硬化剤である前記［１］〜［５］のいずれか記載の着色硬化性樹脂組成物。

［式（２）中、Ｙ^１は、水素原子又は炭素数１〜４のアルキル基を表す。］
［７］前記［１］〜［６］のいずれか記載の着色硬化性樹脂組成物を用いて形成される塗膜。
［８］前記［１］〜［６］のいずれか記載の着色硬化性樹脂組成物を用いて形成されるカラーフィルタ。 That is, the present invention provides the following [1] to [8].
[1] A colored curable resin composition containing a colorant (A), a binder resin (B), a photosensitizer (C), a curing agent (D), a solvent (E), and triphenylphosphine (F).
[2] The colored curable resin composition according to [1], wherein the colorant (A) is a colorant containing a compound represented by the formula (1).

In Expression ^(1), R 1 ~R ⁴ each independently represent a hydrogen atom, -R ⁶ or an aromatic hydrocarbon group having 6 to 10 carbon atoms. The hydrogen atom contained in the aromatic hydrocarbon group is a halogen atom, —R ⁶ , —OH, —OR ⁶ , —SO ₃ ^— , —SO ₃ H, SO ₃ M, —CO ₂ H, —CO ₂ R. ⁶ , may be substituted with —SO ₃ R ⁶ , —SO ₂ NHR ⁸ or —SO ₂ NR ⁸ R ⁹ .
R ⁵ represents —SO ₃ ^— , —SO ₃ H, SO ₃ M, —CO ₂ H, —CO ₂ R ⁶ , —SO ₃ R ⁶ , —SO ₂ NHR ⁸ or —SO ₂ NR ⁸ R ⁹ . .
m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ⁵ may be the same or different.
X represents a halogen atom.
a represents an integer of 0 or 1.
R ⁶ represents a saturated hydrocarbon group having 1 to 10 carbon atoms. A hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom. The methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom, a carbonyl group or —NR ⁷ —.
R ⁷ represents a C 1-10 saturated hydrocarbon group. A hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom. The methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or a carbonyl group.
R ⁸ and R ⁹ each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q. Alternatively, R ⁸ and R ⁹ may be bonded to each other to form a heterocyclic ring having 1 to 10 carbon atoms.
Q represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms, and a hydrogen atom contained in the aromatic hydrocarbon group and the aromatic heterocyclic group is —OH , —R ⁶ , —OR ⁶ , —NO ₂ , —CH═CH ₂ , —CH═CHR ⁶ or a halogen atom.
The hydrogen atom contained in the linear or branched alkyl group having 1 to 10 carbon atoms and the cycloalkyl group having 3 to 30 carbon atoms is a hydroxyl group, a halogen atom, -Q, -CH = CH ₂ or -CH = CHR ⁶ . May be substituted. The methylene group contained in the linear or branched alkyl group having 1 to 10 carbon atoms and the cycloalkyl group having 3 to 30 carbon atoms may be substituted with an oxygen atom, a carbonyl group or —NR ⁶ —. The hydrogen atom contained in the heterocyclic ring having 1 to 10 carbon atoms may be substituted with —R ⁶ , —OH or —Q.
M represents a sodium atom or a potassium atom. ]
[3] The colored curable resin composition according to [1] or [2], wherein the content of triphenylphosphine (F) is 2 to 7% by mass with respect to the solid content of the colored curable resin composition. .
[4] Any of [1] to [3], wherein the solvent (E) is a solvent comprising at least two solvents selected from the group consisting of ethyl lactate, propylene glycol monomethyl ether and diacetone alcohol. Colored curable resin composition.
[5] The colored curable resin composition according to any one of [1] to [4], wherein the photosensitizer (C) is naphthoquinone diazide sulfonic acid ester.
[6] The colored curable resin composition according to any one of [1] to [5], wherein the curing agent (D) is a curing agent having two or more divalent groups represented by the formula (2). .

Wherein (2), ^{Y 1} represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ]
[7] A coating film formed using the colored curable resin composition according to any one of [1] to [6].
[8] A color filter formed using the colored curable resin composition according to any one of [1] to [6].

    According to the colored curable resin composition of the present invention, a coating film that does not cause uneven development can be formed.

Hereinafter, the present invention will be described in detail.
The colored curable resin composition of the present invention contains a colorant (A).

  The colorant (A) used in the colored curable resin composition of the present invention is not particularly limited, and usually the colorant used in the colored curable resin composition can be used. It is preferable that it is a coloring agent containing the compound represented by following formula (1).

The substituents R ^{1 to} R ⁴ in the compound represented by the formula (1) each independently represent a hydrogen atom, —R ^6, or an aromatic hydrocarbon group having 6 to 10 carbon atoms.

Here, the ^{R 6} represents a saturated hydrocarbon group having 1 to 10 carbon atoms. In addition, the hydrogen atom contained in the saturated hydrocarbon group having 1 to 10 carbon atoms may be substituted with a halogen atom, the methylene group is an oxygen atom, a carbonyl group, or —NR ⁷ — (R ⁷ is carbon Represents a saturated hydrocarbon group having 1 to 10. The hydrogen atom contained in the saturated hydrocarbon group having 1 to 10 carbon atoms may be substituted with a halogen atom, and the methylene group is an oxygen atom or a carbonyl group. May be substituted).

-R ⁶ includes, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, isopentyl group, neopentyl group, cyclopentyl group, hexyl group, cyclohexyl group, heptyl group, cycloheptyl group Octyl group, 2-ethylhexyl group, cyclooctyl group, nonyl group, decanyl group, tricyclodecanyl group, methoxypropyl group, ethoxypropyl group, hexyloxypropyl group, 2-ethylhexyloxypropyl group, methoxyhexyl group, An ethoxypropyl group etc. are mentioned.

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms in the substituents R ^{1 to} R ⁴ include a phenyl group and a naphthyl group.

The hydrogen atoms contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms in the substituent ^R 1 to R ⁴ is a halogen _{^{atom, -R 6, -OH, -OR 6}} , -SO 3 -, -SO 3 H, SO ₃ M, —CO ₂ H, —CO ₂ R ⁶ , —SO ₃ R ⁶ , —SO ₂ NHR ⁸ or —SO ₂ NR ⁸ R ⁹ may be substituted.

Here, R ⁶ represents the same meaning as described above.
R ⁸ and R ⁹ are each independently a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q (Q is an aromatic group having 6 to 10 carbon atoms). A hydrocarbon group or a C5-C10 aromatic heterocyclic group is represented, and the hydrogen atom contained in these represents —OH, —R ⁶ , —OR ⁶ , —NO ₂ , —CH═CH ₂ , —CH═. CHR ⁶ or a halogen atom may be substituted.)
The hydrogen atom contained in the linear or branched alkyl group having 1 to 10 carbon atoms and the cycloalkyl group having 3 to 30 carbon atoms in R ⁸ and R ⁹ is —OH, halogen atom, —Q, —CH═CH. ₂ or -CH = CHR ⁶ may be substituted, and the methylene group may be substituted with an oxygen atom, a carbonyl group or -NR ^6- .
R ⁸ and R ⁹ may be bonded to each other to form a heterocyclic ring having 1 to 10 carbon atoms. In this case, the hydrogen atom contained in the heterocyclic ring having 1 to 10 carbon atoms may be substituted with —R ⁶ , —OH or —Q.
The above M represents a sodium atom or a potassium atom.

Examples of the halogen atom that may be substituted for the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms in the substituents R ^{1 to} R ⁴ include a fluorine atom, a chlorine atom, and a bromine atom.

-OR ⁶ includes, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentyloxy group, an n-hexyloxy group, Examples include heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group and the like.

Examples of —CO ₂ R ⁶ include a methyloxycarbonyl group, an ethyloxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butyloxycarbonyl group, an isobutyloxycarbonyl group, a pentyloxycarbonyl group, and an isopentyloxycarbonyl group. , Neopentyloxycarbonyl group, cyclopentyloxycarbonyl group, hexyloxycarbonyl group, cyclohexyloxycarbonyl group, heptyloxycarbonyl group, cycloheptyloxycarbonyl group, octyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, cyclooctyloxycarbonyl group , Nonyloxycarbonyl group, decanyloxycarbonyl group, tricyclodecanyloxycarbonyl group, methoxypropyloxycarbonyl Boniru group, ethoxypropyl oxycarbonyl group, hexyloxy propyloxy group, 2-ethylhexyloxy propyloxy carbonyl group, and the like methoxy hexyloxy group.

Examples of —SO ₃ R ⁶ include a methanesulfonyl group, an ethanesulfonyl group, a hexanesulfonyl group, and a decanesulfonyl group.

—SO ₂ NHR ⁸ includes sulfamoyl group, methanesulfamoyl group, ethanesulfamoyl group, propanesulfamoyl group, isopropanesulfamoyl group, butanesulfamoyl group, isobutanesulfamoyl group, pentanesulfa. Moyl group, isopentanesulfamoyl group, neopentanesulfamoyl group, cyclopentanesulfamoyl group, hexanesulfamoyl group, cyclohexanesulfamoyl group, heptanesulfamoyl group, cycloheptanesulfamoyl group, octanesl Famoyl group, 2-ethylhexanesulfamoyl group, 1,5-dimethylhexanesulfamoyl group, cyclooctanesulfamoyl group, nonanesulfamoyl group, decanesulfamoyl group, tricyclodecanesulfamoyl group, methoxy Professional N-sulfamoyl group, ethoxypropanesulfamoyl group, propoxypropanesulfamoyl group, isopropoxypropanesulfamoyl group, hexyloxypropanesulfamoyl group, 2-ethylhexyloxypropanesulfamoyl group, methoxyhexanesulfamoyl group And 3-phenyl-1-methylpropanesulfamoyl group.

Furthermore, examples of —SO ₂ NHR ⁸ include groups represented by the following formulae.

In the above compound exemplified as —SO ₂ NHR ⁸ , X ¹ represents a halogen atom, and X ² represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a halogen atom or Represents a nitro group. X ³ represents an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms. Furthermore, the hydrogen atom of the alkyl group and alkoxy group in X ² and X ³ may be substituted with a halogen atom.

Examples of the halogen atom in X ¹ , X ² and X ³ include a fluorine atom, a chlorine atom and a bromine atom.
Examples of the alkyl group having 1 to 3 carbon atoms that may be substituted with a halogen atom include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a perfluoromethyl group.
Examples of the alkoxy group having 1 to 3 carbon atoms which may be substituted with a halogen atom include a methoxy group, an ethoxy group and a propoxy group.

Among them, as —SO ₂ NHR ⁸ , R ⁸ is a branched alkyl group having 6 to 8 prime numbers, an alicyclic alkyl group having 5 to 7 carbon atoms, an allyl group, a phenyl group, and an aralkyl group having 8 to 10 carbon atoms. , Those having a C2-C8 hydroxyl group-containing alkyl group and aryl group, or a C2-C8 alkoxy group-containing alkyl group or aryl group are preferred, and those having a 2-ethylhexyl group are particularly preferred.

Examples of —SO ₂ NR ⁸ R ⁹ include a group represented by the following formula.

In the above compound exemplified as —SO ₂ NR ⁸ R ⁹ , X ² represents the same meaning as described above.

Among them, as —SO ₂ NR ⁸ R ⁹ , R ⁸ and R ⁹ are a branched alkyl group having 6 to 8 carbon atoms, an alicyclic alkyl group having 5 to 7 carbon atoms, an allyl group, a phenyl group, and a carbon number. Those having 8 to 10 aralkyl groups, C 2-8 hydroxyl group-containing alkyl and aryl groups, or C 2-8 alkoxy group-containing alkyl or aryl groups are preferred, and those having 2-ethylhexyl groups are particularly preferred. .

Examples of the substituent of the aromatic hydrocarbon group having 6 to 10 carbon atoms in the substituents R ^{1 to} R ⁴ in the formula (1) include an ethyl group, a propyl group, a phenyl group, a dimethylphenyl group, —SO ₃ R ^6. or _-SO 2 NHR ⁸ is preferred.

  Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms having a substituent include methylphenyl group, dimethylphenyl group, trimethylphenyl group, ethylphenyl group, hexylphenyl group, decanylphenyl group, fluorophenyl group, chlorophenyl group, Examples thereof include a bromophenyl group, a hydroxyphenyl group, a methoxyphenyl group, a dimethoxyphenyl group, an ethoxyphenyl group, a hexyloxyphenyl group, a decanyloxyphenyl group, and a trifluoromethylphenyl group.

In the substituents R ^{1 to} R ⁴ in the formula (1), at least one of R ¹ and R ² or at least one of R ³ and R ⁴ is an alkyl group having 1 to 4 carbon atoms. Or it is preferable that it is a C6-C10 aromatic hydrocarbon group which may be substituted.
Further, at least one of R ¹ and R ² and at least one of R ³ and R ⁴ is an alkyl group having 1 to 4 carbon atoms or an optionally substituted fragrance having 6 to 10 carbon atoms. It is preferably a group hydrocarbon group, and in particular, at least one of R ¹ and R ² and at least one of R ³ and R ⁴ may have 6 to 10 carbon atoms which may be substituted. It is more preferably an aromatic hydrocarbon group.

The substituent R ⁵ in the compound represented by the formula (1) is —SO ₃ ^— , —SO ₃ H, SO ₃ M, —CO ₂ H, —CO ₂ R ⁶ , —SO ₃ R ⁶ , —SO _2. NHR ⁸ or an _-SO 2 ^NR 8 ^{R 9.}
In formula (1), m represents an integer of 0 to 5, and when m is an integer of 2 or more, the plurality of R ⁵ may be the same or different.

R ⁵ is preferably a carboxyl group, an ethyloxycarbonyl group, a sulfoxyl group, a 2-ethylhexyloxypropane sulfamoyl group, a 1,5-dimethylhexanesulfamoyl group, or 3-phenyl-1-methylpropanesulfa. A moyl group and an isopropoxypropane sulfamoyl group are mentioned.

In formula (1), X represents a halogen atom, and a represents an integer of 0 or 1.
Examples of the halogen atom represented by X include a fluorine atom, a chlorine atom and a bromine atom.

  The compound represented by the formula (1) is preferably a compound represented by the following formula (1-1) or (1-2).

［式（１−１）中、Ｒ^１１〜Ｒ^１４は、それぞれ独立に、水素原子、−Ｒ^６又は炭素数６〜１０の芳香族炭化水素基を表す。該炭素数６〜１０の芳香族炭化水素基に含まれる水素原子は、ハロゲン原子、−Ｒ^６、−ＯＨ、−ＯＲ^６、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、−ＳＯ_３Ｎａ、−ＣＯ_２Ｈ、−ＣＯ_２Ｒ^６、−ＳＯ_３Ｒ^６、−ＳＯ_２ＮＨＲ^８又は−ＳＯ_２ＮＲ^８Ｒ^９で置換されていてもよい。
Ｒ^１５は、水素原子、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、−ＳＯ_２ＮＨＲ^８又は−ＳＯ_２ＮＲ^８Ｒ^９を表す。
Ｒ^１６は、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、−ＳＯ_２ＮＨＲ^８又は−ＳＯ_２ＮＲ^８Ｒ^９を表す。
Ｒ^６、Ｒ^８、Ｒ^９、ｍ、Ｘ及びａは、前記と同じ意味を表す。］

[In Formula (1-1), R ^{11 to} R ¹⁴ each independently represents a hydrogen atom, —R ^6, or an aromatic hydrocarbon group having 6 to 10 carbon atoms. The hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms is a halogen atom, —R ⁶ , —OH, —OR ⁶ , —SO ₃ ^— , —SO ₃ H, —SO ₃ Na, —CO _It may be substituted with ₂ H, —CO ₂ R ⁶ , —SO ₃ R ⁶ , —SO ₂ NHR ⁸ or —SO ₂ NR ⁸ R ⁹ .
R ¹⁵ represents a hydrogen atom, —SO ₃ ^— , —SO ₃ H, —SO ₂ NHR ⁸ or —SO ₂ NR ⁸ R ⁹ .
R ¹⁶ represents —SO ₃ ^— , —SO ₃ H, —SO ₂ NHR ⁸ or —SO ₂ NR ⁸ R ⁹ .
R ⁶ , R ⁸ , R ⁹ , m, X and a represent the same meaning as described above. ]

［式（１−２）中、Ｒ^２１〜Ｒ^２４は、それぞれ独立に、水素原子、−Ｒ^２６又は炭素数６〜１０の芳香族炭化水素基を表す。該炭素数６〜１０の芳香族炭化水素基に含まれる水素原子は、ハロゲン原子、−Ｒ^２６、−ＯＨ、−ＯＲ^２６、−ＳＯ_３ ⁻、−ＳＯ_３Ｎａ、−ＣＯ_２Ｈ、−ＣＯ_２Ｒ^２６、−ＳＯ_３Ｈ、−ＳＯ_３Ｒ^２６又は−ＳＯ_２ＮＨＲ^２８で置換されていてもよい。
Ｒ^２５は、−ＳＯ_３ ⁻、−ＳＯ_３Ｎａ、−ＣＯ_２Ｈ、−ＣＯ_２Ｒ^２６、−ＳＯ_３Ｈ又は−ＳＯ_２ＮＨＲ^２８を表す。
Ｒ^２６は、炭素数１〜１０の飽和炭化水素基を表す。該炭素数１〜１０の飽和炭化水素基に含まれる水素原子は、−ＯＲ^２７又はハロゲン原子で置換されていてもよい。
Ｒ^２７は、炭素数１〜１０の飽和炭化水素基を表す。該炭素数１〜１０の飽和炭化水素基に含まれる水素原子は、ハロゲン原子で置換されていてもよい。
Ｒ^２８は、水素原子、−Ｒ^２６、−ＣＯ_２Ｒ^２６又は炭素数６〜１０の芳香族炭化水素基を表し、該炭素数６〜１０の芳香族炭化水素基に含まれる水素原子は、−Ｒ^２６又は−ＯＲ^２６で置換されていてもよい。
ｍ、Ｘ及びａは、前記と同じ意味を表す。］

[In Formula (1-2), R ^{21 to} R ²⁴ each independently represents a hydrogen atom, —R ^26, or an aromatic hydrocarbon group having 6 to 10 carbon atoms. Hydrogen atoms contained in the aromatic hydrocarbon group of carbon number 6-10, a halogen _{^{atom, -R 26, -OH, -OR 26}} , -SO 3 -, -SO 3 Na, -CO 2 H, -CO ₂ R _{^26, -SO} 3 _H, optionally substituted by -SO ^{3 R 26} or _-SO 2 ^{NHR 28.}
R ²⁵ represents —SO ₃ ^— , —SO ₃ Na, —CO ₂ H, —CO ₂ R ²⁶ , —SO ₃ H or —SO ₂ NHR ²⁸ .
R ²⁶ represents a saturated hydrocarbon group having 1 to 10 carbon atoms. The hydrogen atom contained in the saturated hydrocarbon group having 1 to 10 carbon atoms may be substituted with —OR ²⁷ or a halogen atom.
R ²⁷ represents a saturated hydrocarbon group having 1 to 10 carbon atoms. A hydrogen atom contained in the saturated hydrocarbon group having 1 to 10 carbon atoms may be substituted with a halogen atom.
R ²⁸ represents a hydrogen atom, —R ²⁶ , —CO ₂ R ²⁶ or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms is it may be substituted by -R ²⁶ or ^{-OR 26.}
m, X, and a represent the same meaning as described above. ]

  Furthermore, the compound represented by the formula (1) is preferably a compound represented by the following formula (1-3).

［式（１−３）中、Ｒ^３１及びＲ^３２は、それぞれ独立に、フェニル基を表す。該フェニル基に含まれる水素原子は、ハロゲン原子、−Ｒ^２６、−ＯＲ^２６、−ＣＯ_２Ｒ^２６、−ＳＯ_３Ｒ^２６又は−ＳＯ_２ＮＨＲ^２８で置換されていてもよい。
Ｒ^３３は、−ＳＯ_３ ⁻又は−ＳＯ_２ＮＨＲ^２８を表す。
Ｒ^３４は、水素原子、−ＳＯ_３ ⁻又は−ＳＯ_２ＮＨＲ^２８を表す。
Ｒ^２６、Ｒ^２８、Ｘ及びａは、前記と同じ意味を表す。］

[In Formula (1-3), R ³¹ and R ³² each independently represent a phenyl group. The hydrogen atom contained in the phenyl group may be substituted with a halogen atom, —R ²⁶ , —OR ²⁶ , —CO ₂ R ²⁶ , —SO ₃ R ^26, or —SO ₂ NHR ²⁸ .
R ³³ represents —SO ₃ ^— or —SO ₂ NHR ²⁸ .
R ³⁴ represents a hydrogen atom, —SO ₃ ^— or —SO ₂ NHR ²⁸ .
R ²⁶ , R ²⁸ , X and a have the same meaning as described above. ]

  Furthermore, the compound represented by the formula (1) is more preferably a compound represented by the following formula (1-4).

［式（１−４）中、Ｒ^４１及びＲ^４２は、それぞれ独立に、フェニル基を表す。該フェニル基に含まれる水素原子は、−Ｒ^２６又は−ＳＯ_２ＮＨＲ^２８で置換されていてもよい。
Ｒ^４３は、−ＳＯ_３ ⁻又は−ＳＯ_２ＮＨＲ^２８を表す。
Ｒ^２６、Ｒ^２８、Ｘ及びａは、前記と同じ意味を表す。］

[In Formula (1-4), R ⁴¹ and R ⁴² each independently represent a phenyl group. The hydrogen atom contained in the phenyl group may be substituted with —R ²⁶ or —SO ₂ NHR ²⁸ .
R ⁴³ represents —SO ₃ ^— or —SO ₂ NHR ²⁸ .
R ²⁶ , R ²⁸ , X and a have the same meaning as described above. ]

  Examples of the compound represented by the formula (1) include compounds represented by the following formulas (1a) to (1f).

［式（１ａ）中、Ｒ^５１及びＲ^５２は、それぞれ独立に、水素原子、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ、−ＣＯ_２Ｈ又は−ＳＯ_２ＮＨＲ^５０を表す。Ｒ^５０は、２−エチルヘキシルを表す。Ｘ及びａは、上記と同じ意味を表す。］

[In Formula (1a), R ⁵¹ and R ⁵² each independently represent a hydrogen atom, —SO ₃ ^— , —SO ₃ H, —CO ₂ H, or —SO ₂ NHR ⁵⁰ . R ⁵⁰ represents 2-ethylhexyl. X and a represent the same meaning as described above. ]

［式（１ｂ）中、Ｒ^５１は、上記と同じ意味を表す。］

[In formula (1b), R ⁵¹ represents the same meaning as described above. ]

［式（１ｂ−１）中、Ｒ^５１、Ｘ及びａは、上記と同じ意味を表す。] The compound represented by the formula (1b) is a tautomer of the compound represented by the formula (1b-1).

[In formula (1b-1), R ⁵¹ , X and a represent the same meaning as described above. ]

[式（１ｃ）及び式（１ｄ）中、Ｒ^５３、Ｒ^５４及びＲ^５５は、それぞれ独立に、−ＳＯ_３ ⁻、−ＳＯ_３Ｎａ又は−ＳＯ_２ＮＨＲ^５０を表す。Ｒ^５０は、２−エチルヘキシルを表す。]

[In Formula (1c) and Formula (1d), R ⁵³ , R ⁵⁴ and R ⁵⁵ each independently represent —SO ₃ ^— , —SO ₃ Na or —SO ₂ NHR ⁵⁰ . R ⁵⁰ represents 2-ethylhexyl. ]

[式（１ｅ）及び式（１ｆ）中、Ｒ^５６、Ｒ^５７及びＲ^５８は、それぞれ独立に、水素原子、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ又は−ＳＯ_２ＮＨＲ^５０を表す。Ｒ^５０は、２−エチルヘキシルを表す。]

[In formula (1e) and formula (1f), R ⁵⁶ , R ⁵⁷ and R ⁵⁸ each independently represent a hydrogen atom, —SO ₃ ^— , —SO ₃ H or —SO ₂ NHR ⁵⁰ . R ⁵⁰ represents 2-ethylhexyl. ]

Specific examples of the compound represented by the formula (1a) to the formula (1f) include a compound obtained by sulfonamidating sulforhodamine B, —SO ₃ ^{— of} sulforhodamine B, or —SO ₃ H; I. Solvent Red 49, Rhodamine B, C.I. I. Acid Violet 102, C.I. I. A compound obtained by sulfonamidation of —SO ₃ ^— or —SO ₃ H of Acid Violet 102, C.I. I. Acid Red 289, C.I. I. And compounds obtained by sulfonamidating Acid Red 289 —SO ₃ ^— or —SO ₃ H. The colorant (A) of the present invention is preferably a compound represented by the formula (1e) or the formula (1f). I. Acid Red 289, C.I. I. A compound obtained by sulfonamidating Acid Red 289 —SO ₃ ^— or —SO ₃ H is preferred. In particular, a compound represented by the formula (AI) is preferable.

The compound represented by formula (1) is obtained by, for example, chlorinating a dye or dye intermediate having —SO ₃ H by a conventional method, and converting the obtained dye or dye intermediate having —SO ₂ Cl into R ⁸ —NH. It can manufacture by making it react with the amine represented by ₂ . Moreover, it can manufacture by making the pigment | dye manufactured by the method of Unexamined-Japanese-Patent No. 3-78702 page 3 right upper column-lower left column react with an amine after chlorination like the above.

  When the colorant (A) is a colorant containing a compound represented by the formula (1), the colorant (A) is a colorant containing a compound represented by the formula (1) (hereinafter referred to as “coloring”). In addition to “agent (A1)”, it may be a colorant containing another colorant. Examples of other colorants include dyes and pigments. A dye is preferred.

Examples of the dye include acid dyes, basic dyes, direct dyes, sulfur dyes, vat dyes, naphthol dyes, reactive dyes, and disperse dyes, and can be selected from known dyes for conventional color filter applications.
Specifically, for example, C.I. I. Solvent Yellow 4, 14, 15, 24, 82, 94, 98, 162; C.I. I. Solvent Red 45;
C. I. Solvent Orange 2, 7, 11, 15, 26, 56;
C. I. Solvent Blue 35, 37, 59, 67;
C. I. Acid Yellow 17, 29, 40, 76;
C. I. Acid Red 91, 92, 97, 114, 138, 151;
C. I. Acid Orange 51, 63;
C. I. Acid Blue 80, 83, 90;
C. I. Acid Green 9, 16, 25, 27;
C. I. Basic red 1 and the like, preferably C.I. I. Solvent Yellow 82, 162, C.I. I. Solvent Red 45, C.I. I. Solvent Orange 56, C.I. I. Solvent Blue 6, C.I. I. Acid Blue 90, C.I. I. Acid Green 9, 16, C.I. I. Basic Red 1 etc. are mentioned.

Examples of the pigment include organic pigments and inorganic pigments, and compounds classified as pigments in the color index (published by The Society of Dyers and Colorists).
Specifically, for example, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 55, 60, 65, 73, 74, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 116, 117, 119, 120, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, Yellow pigments such as 151, 152, 153, 154, 156, 166, 173, 175, 194, 214;
C. I. Pigment Orange 2, 5, 13, 16, 17: 1, 31, 34, 36, 38, 40, 42, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 64, 65, Orange pigments such as 71, 73;
C. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48: 1, 48: 2, 48: 3, 48: 4, 49, 49: 1, 49: 2, 52: 1, 52: 2, 53: 1, 57: 1, 60: 1, 63: 1, 66, 67, 81: 1, 81: 3, 81, 83, 88, 90, 97, 112, 119, 105, 122, 123, 144, 146, 149, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 180, 184, 185, Red pigments such as 187, 188, 190, 192, 200, 202, 206, 207, 208, 209, 210, 215, 216, 224, 226, 242, 254, 255, 264, 265;
C. I. Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60;
C. I. Violet color pigments such as CI Pigment Violet 1, 3, 5: 1, 19, 23, 27, 29, 32, 36, 38, 42;
C. I. Green pigments such as CI Pigment Green 1, 2, 4, 7, 36, 58;
C. I. Brown pigments such as CI Pigment Brown 23 and 25;
C. I. And black pigments such as CI Pigment Black 1 and 7. Among them, C.I. I. Pigment yellow 138, 139, 150, C.I. I. Pigment red 177, 242, 254, C.I. I. Pigment red violet 23, C.I. I. Pigment blue 15: 6 and C.I. I. It is preferable to contain at least one pigment selected from CI Pigment Green 36 and 58. These pigments may be used alone or in combination of two or more.

  Among the above pigments, organic pigments may be rosin-treated, surface treatment using a pigment derivative or pigment dispersant into which an acidic group or basic group is introduced, or grafting to the pigment surface with a polymer compound, if necessary. Treatment, atomization by sulfuric acid atomization, or the like, cleaning by an organic solvent or water for removing impurities, removal by ion exchange of ionic impurities, or the like may be performed.

  As the pigment dispersant, commercially available surfactants can be used, and examples include silicone-based, fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, and amphoteric surfactants. Each is used alone or in combination of two or more. Examples of the surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, and polyethyleneimines. Other trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow (manufactured by Kyoei Chemical Co., Ltd.), F-Top (manufactured by Tochem Products), Megafuck (manufactured by DIC Corporation), and Florard (Sumitomo 3M). Manufactured by Asahi Guard, Surflon (manufactured by Asahi Glass Co., Ltd.), Solsperse (manufactured by GENECA), EFKA (manufactured by EFKA CHEMICALS), PB821 (manufactured by Ajinomoto Co., Inc.), Disperbyk (Bicchemy) Manufactured).

The colorant (A1) and other colorants can be used alone or in combination of two or more. Moreover, a coloring agent (A1) and another coloring agent can be mixed and used by arbitrary ratios. In that case, the mixing ratio of the colorant (A1) and the other colorant is preferably in the following range in terms of mass ratio.
Colorant (A1); 20 to 60% by mass
Other colorants: 40 to 80% by mass

  When the mixing ratio of the colorant (A1) and other colorants is within the above range, the desired spectrum can be obtained, which is preferable.

  Content of a coloring agent (A) is a mass fraction with respect to solid content in a colored curable resin composition, Preferably it is 1-75 mass%, More preferably, it is 10-70 mass%, Furthermore, Preferably it is 20-65 mass%. Here, solid content means the total amount of the component remove | excluding the solvent from the colored curable resin composition. When the content of the colorant (A) is in the above range, the desired spectrum can be obtained, which is preferable.

  The colored curable resin composition of the present invention contains a binder resin (B).

  It does not specifically limit as binder resin (B) used for the colored curable resin composition of this invention, Usually, what is used for a colored curable resin composition can be used. Among them, an alkali-soluble resin that can be dissolved in an alkaline developer is preferable, and examples thereof include a resin having a carboxy group and a resin having a hydroxy group (particularly a phenolic hydroxyl group). These can be used alone or in combination of two or more.

Examples of such alkali-soluble resins include novolak resins of p-cresol, novolak resins of p-cresol and m-cresol, novolac resins having a structure represented by the following formula (3), polyvinyl Examples thereof include phenol and a copolymer of styrene and vinylphenol. Among these, novolac resin is preferable. These can be used alone or in combination of two or more.

  As the binder resin (B), for example, Marka Linker M, Marka Linker CST-15, Marka Linker CST-70 (manufactured by Maruzen Petrochemical Co., Ltd.), Hitanol 1501 (manufactured by Hitachi Chemical Co., Ltd.), tackolol 101 (Taoka) Chemical Industry Co., Ltd.), Tamanoru 7508 (Arakawa Chemical Industry Co., Ltd.), PSM-4261, PSM-4324, PSM-4327, PSM-4326 (all manufactured by Gunei Chemical Co., Ltd.), CRG-951 Commercial products such as Showa Polymer Co., Ltd. may be used.

  Although the molecular weight of binder resin (B) is not specifically limited, For example, as a weight average molecular weight of polystyrene conversion, it is preferable that it is about 3,000-100,000, Furthermore, about 5,000-50,000. . When the weight average molecular weight of the binder resin (B) is in the above range, the coating property tends to be good, the film is not easily reduced during development, and the non-pixel part is easily removed during development. It tends to be preferable.

  Content of binder resin (B) is a mass fraction with respect to solid content in a colored curable resin composition, Preferably it is 1-50 mass%, More preferably, it is 1-20 mass%. When the content of the binder resin (B) is in the above range, the solubility of the exposed portion in the image liquid and the shape of the pattern tend to be favorable, which is preferable.

  The colored curable resin composition of the present invention contains a photosensitizer (C).

  As a photosensitizer (C), it does not specifically limit and what is normally used for colored curable resin composition can be used. Examples include o-benzoquinone diazide sulfonic acid ester, o-naphthoquinone diazide sulfonic acid ester, o-benzoquinone diazide sulfonic acid amide, o-naphthoquinone diazide sulfonic acid amide, etc. A compound having a quinonediazide group is preferred, and o-naphthoquinonediazidesulfonic acid ester is particularly preferred. These can be used alone or in combination of two or more.

  Examples of the compound having a naphthoquinone diazide group include an ester compound of an o-naphthoquinone diazide sulfonic acid compound and at least one phenol compound selected from the group consisting of the following formulas (I) to (V), and these ester compounds. Or a mixture of two or more thereof.

  Examples of the o-naphthoquinone diazide sulfonic acid compound include o-naphthoxynone diazide-5-sulfonic acid and o-naphthoxynone diazide-4-sulfonic acid.

  Content of a photosensitizer (C) is a mass fraction with respect to solid content in a colored curable resin composition, Preferably it is 1-40 mass%, More preferably, it is 10-40 mass%. When the content of the photosensitizer (C) is within the above range, the difference in dissolution rate between the unexposed area and the exposed area tends to be high, which tends to maintain a high development residual film ratio, which is preferable.

  The colored curable resin composition of the present invention contains a curing agent (D).

  As a hardening | curing agent (D), it does not specifically limit, Although what is normally used for a colored curable resin composition can be used, The heat-hardening agent hardened | cured by heating is suitable especially.

Examples of such a curing agent include melamine compounds and compounds of the following formulas (i) to (vi).

［式（２）中、Ｙ^１は、水素原子又は炭素数１〜４のアルキル基を表す。］ In particular, the curing agent (D) contained in the colored curable resin composition of the present invention is preferably a compound having two or more divalent groups represented by the following formula (2).

Wherein (2), ^{Y 1} represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ]

  Specific examples of such compounds include hexamethoxymethylmelamine and compounds represented by the above formulas (iii), (iv), (v), and (vi).

  Content of a hardening | curing agent (D) is a mass fraction with respect to solid content in a colored curable resin composition, Preferably it is 1-30 mass%, More preferably, it is 10-30 mass%. When the content of the curing agent (D) is in the above range, the coating film formed from the colored curable resin composition or the resistance of the pattern to the solvent tends to be favorable, which is preferable.

  The colored curable resin composition of the present invention contains a solvent (E).

The solvent (E) contained in the colored curable resin composition of the present invention is preferably a solvent comprising at least two solvents selected from the group consisting of ethyl lactate, propylene glycol monomethyl ether and diacetone alcohol. .
That is, a mixed solvent of ethyl lactate and propylene glycol monomethyl ether, a mixed solvent of ethyl lactate and diacetone alcohol, a mixed solvent of propylene glycol monomethyl ether and diacetone alcohol, and ethyl lactate, propylene glycol monomethyl ether and diacetone alcohol And a mixed solvent. Among these, a mixed solvent containing ethyl lactate is more preferable.

Ethyl lactate, propylene glycol monomethyl ether and diacetone alcohol can be mixed and used at an arbitrary ratio.
In particular, the content of ethyl lactate is preferably 10 to 90% by mass and more preferably 15 to 85% by mass with respect to the total amount of the solvent (E).
In addition, the content of at least one solvent selected from the group consisting of propylene glycol monomethyl ether and diacetone alcohol is preferably 10 to 90% by mass with respect to the total amount of the solvent (E), and further 15 to 15%. More preferably, it is 85 mass%.

  By using such a mixed solvent, compatibility with each component of the colored curable resin composition is ensured, and it is sometimes called a spin coater, a slit & spin coater, a slit coater (a die coater or a curtain flow coater). .) Effectively preventing the generation of streaks even when applied on an uneven substrate by various application methods, particularly spin application methods, using various application devices such as inkjet, roll coater, dip coater, etc. be able to.

The solvent (E) is preferably composed of only the solvents described above, but may contain other solvents as long as the effects of the present invention are not impaired. As the other solvent, various solvents usually used in the colored curable resin composition can be used, and examples thereof include alcohols such as monoalcohol and polyhydric alcohol.
As such alcohol, specifically, methanol, ethanol, propanol, butanol, pentanol, hexanol, cyclohexanol, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol propyl ether, ethylene glycol, ethylene glycol monomethyl ether, Examples include ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, methyl lactate, 2-methyl methyl lactate, 3-methoxybutanol, and glycerin.

And ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether and ethylene glycol monobutyl ether;
Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monoethyl ether acetate;
Alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, methoxypentyl acetate;
Propylene glycol monoalkyl ethers such as propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether;
Propylene glycol dialkyl ethers such as propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol ethyl methyl ether, propylene glycol dipropyl ether, propylene glycol propyl methyl ether, propylene glycol ethyl propyl ether, propylene glycol methyl ether propionate, propylene glycol ethyl ether Propylene glycol alkyl ether propionates such as propionate, propylene glycol propyl ether propionate, propylene glycol butyl ether propionate;
Butyldiol monoalkyl ethers such as methoxybutyl alcohol, ethoxybutyl alcohol, propoxybutyl alcohol, butoxybutyl alcohol;
Butanediol monoalkyl ether acetates such as methoxybutyl acetate, ethoxybutyl acetate, propoxybutyl acetate, butoxybutyl acetate;
Butanediol monoalkyl ether propionates such as methoxybutyl propionate, ethoxybutyl propionate, propoxybutyl propionate, butoxybutyl propionate;
Dipropylene glycol dialkyl ethers such as dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol methyl ethyl ether;
Aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene;
Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone;
Methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl 2-hydroxypropionate, methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, methyl hydroxyacetate, hydroxyethyl acetate, hydroxy Butyl acetate, methyl lactate, propyl lactate, butyl lactate, methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, propyl 3-hydroxypropionate, butyl 3-hydroxypropionate, methyl 2-hydroxy-3-methylbutanoate, Methyl methoxyacetate, ethyl methoxyacetate, propyl methoxyacetate, butyl methoxyacetate, methyl ethoxy acetate, ethyl ethoxy acetate, propyl ethoxy acetate, butyl ethoxy acetate, methyl propoxyacetate, ethyl propoxyacetate Propoxy propyl acetate, butyl propoxy acetate, methyl butoxy acetate, butoxy acetate ethyl, butoxy acetate propyl, butoxy acetate butyl, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, 2-methoxypropionic acid Butyl, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, propyl 2-ethoxypropionate, butyl 2-ethoxypropionate, methyl 2-butoxypropionate, ethyl 2-butoxypropionate, propyl 2-butoxypropionate Butyl 2-butoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, butyl 3-methoxypropionate, 3-ethoxyprop Methyl onate, ethyl 3-ethoxypropionate, propyl 3-ethoxypropionate, butyl 3-ethoxypropionate, methyl 3-propoxypropionate, ethyl 3-propoxypropionate, propyl 3-propoxypropionate, 3-propoxypropion Esters such as butyl acid, methyl 3-butoxypropionate, ethyl 3-butoxypropionate, propyl 3-butoxypropionate, butyl 3-butoxypropionate, ethyl pyruvate;
Cyclic ethers such as tetrahydrofuran and pyran;
cyclic esters such as γ-butyrolactone;
Further, it may contain methyl cellosolve, ethyl cellosolve, diethylene glycol dimethyl ether, ethylene glycol monoisopropyl ether, N-methylpyrrolidone, dimethyl sulfoxide, N, N′-dimethylformamide, cyclohexane, propylene glycol monoethyl ether acetate, etc. Good.

  Content of a solvent (E) is a mass fraction with respect to a colored curable resin composition, Preferably it is 10-90 mass%, More preferably, it is 50-90 mass%. When the content of the solvent (E) is in the above range, the coatability tends to be good, which is preferable.

  The colored curable resin composition of the present invention contains triphenylphosphine (F).

  The content of triphenylphosphine (F) is a mass fraction with respect to the solid content of the colored curable resin composition (total amount of components obtained by removing the solvent from the colored curable resin composition), preferably 2 to 7 % By mass. When the content of triphenylphosphine is 2% by mass or more, uneven development tends to be suppressed, which is preferable. Further, from the viewpoint of reducing chemical resistance of the coating film or pattern formed from the colored curable resin composition and decreasing the residual film rate, it is preferably 7% by mass or less, more preferably 6% by mass or less, particularly 4% by mass or less. It is more preferable that

  Various additives such as a filler, a surfactant, an adhesion promoter, an antioxidant, an ultraviolet absorber, a light stabilizer, and a chain transfer agent are added to the colored curable resin composition of the present invention as necessary. You may use together.

Examples of the filler include glass, silica, and alumina.
Examples of other polymer compounds include thermoplastic resins such as curable resins such as epoxy resins and maleimide resins, polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane.

  A commercially available surfactant can be used as the surfactant. The surfactant may be any of surfactants such as silicone, fluorine, ester, cationic, anionic, nonionic, and amphoteric. Specific examples include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethyleneimines, Under the trade names KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow (manufactured by Kyoei Chemical Co., Ltd.), F-Top (manufactured by Tochem Products), MegaFac (manufactured by DIC Corporation), Florard (Sumitomo 3M Co., Ltd.) Asahi Guard, Surflon (manufactured by Asahi Glass Co., Ltd.), Solsperse (manufactured by Geneca Corporation), EFKA (manufactured by EFKA CHEMICALS), PB821 (manufactured by Ajinomoto Co., Inc.), and the like.

  Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, and N- (2-amino). Ethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyl Examples include trimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, and 3-mercaptopropyltrimethoxysilane.

  Examples of the antioxidant include 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate, 2- [1- (2-hydroxy-3). , 5-Di-tert-pentylphenyl) ethyl] -4,6-di-tert-pentylphenyl acrylate, 6- [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propoxy] -2 , 4,8,10-tetra-tert-butyldibenz [d, f] [1,3,2] dioxaphosphine, 3,9-bis [2- {3- (3-tert-butyl-4- Hydroxy-5-methylphenyl) propionyloxy} -1,1-dimethylethyl] -2,4,8,10-tetraoxaspiro [5.5] undecane, 2,2′-methyle Bis (6-tert-butyl-4-methylphenol), 4,4′-butylidenebis (6-tert-butyl-3-methylphenol), 4,4′-thiobis (2-tert-butyl-5-methylphenol) ), 2,2′-thiobis (6-tert-butyl-4-methylphenol), dilauryl 3,3′-thiodipropionate, dimyristyl 3,3′-thiodipropionate, distearyl 3,3′- Thiodipropionate, pentaerythrityltetrakis (3-laurylthiopropionate), 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine -2,4,6 (1H, 3H, 5H) -trione, 3,3 ', 3 ", 5,5', 5" -hexa-tert-butyl-a, a ', ''-(Mesitylene-2,4,6-triyl) tri-p-cresol, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 2,6-di -Tert-butyl-4-methylphenol and the like.

  Examples of the ultraviolet absorber include 2- (2-hydroxy-5-tert-butylphenyl) -2H-benzotriazole, octyl-3- [3-tert-butyl-4-hydroxy-5- (5-chloro-). 2H-benzotriazol-2-yl) phenyl] propionate, 2- [4-[(2-hydroxy-3-dodecyloxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethyl) Phenyl) -1,3,5-triazine, 2- [4-[(2-hydroxy-3- (2′-ethyl) hexyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4 -Dimethylphenyl) -1,3,5-triazine, 2,4-bis (2-hydroxy-4-butyloxyphenyl) -6- (2,4-bis-butyloxyphenyl) 1,3,5-triazine, 2- (2-hydroxy-4- [1-octyloxycarbonylethoxy] phenyl) -4,6-bis (4-phenylphenyl) -1,3,5-triazine, 2- (2H-benzotriazol-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol, 2- (2H-benzotriazol-2-yl) -6- (1-methyl-1- Phenylethyl) -4- (1,1,3,3-tetramethylbutyl) phenol, 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzotriazole, alkoxybenzophenone, etc. Can be mentioned.

  Examples of the light stabilizer include a polymer composed of succinic acid and (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl) ethanol, N, N ′, N ″, N ″. '-Tetrakis (4,6-bis (butyl- (N-methyl-2,2,6,6-tetramethylpiperidin-4-yl) amino) triazin-2-yl) -4,7-diazadecane-1, Reaction product of 10-diamine, decandioic acid, bis (2,2,6,6-tetramethyl-1- (octyloxy) -4-piperidinyl) ester and 1,1-dimethylethyl hydroperoxide Bis (1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methyl] butyl malonate, 2,4 -Bis [N-B Ru-N- (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) amino] -6- (2-hydroxyethylamine) -1,3,5-triazine, bis (1, 2,2,6,6-pentamethyl-4-piperidinyl) sebacate, methyl (1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate and the like.

  Examples of the chain transfer agent include dodecyl mercaptan and 2,4-diphenyl-4-methyl-1-pentene.

  The colored curable resin composition of the present invention forms, for example, a substrate such as a substrate such as a silicon wafer, glass, metal, plastic, a color filter, various insulating or conductive films, a drive circuit, and the like as follows. By applying on these substrates, a coating film can be formed. The coating film is preferably dried and cured. Moreover, the obtained coating film can be patterned into a desired shape and used as a pattern. Furthermore, these coating films or patterns may be formed and used as part of a component such as a display device.

First, the colored curable resin composition of the present invention is applied on a substrate.
As described above, the coating can be performed using various coating apparatuses such as a spin coater, a slit & spin coater, a slit coater, an ink jet, a roll coater, and a dip coater. Among these, for reasons such as solubility, prevention of drying, and prevention of the generation of foreign matter, it is preferable to perform application by spin coating, that is, application using a slit & spin coater or spin coater.

It is then suitable to dry or pre-bake to remove volatile components such as solvents. Thereby, a smooth uncured coating film can be obtained.
As for the temperature of drying or prebaking, about 80-130 degreeC is mentioned, for example. Moreover, the film thickness of a coating film is not specifically limited, It can adjust suitably with the material to be used, a use, etc. For example, about 0.4-2 micrometers is illustrated.

Furthermore, the obtained uncured coating film is irradiated with light, for example, ultraviolet rays generated from a mercury lamp or a light emitting diode, through a mask for forming a target pattern. The shape of the mask at this time is not particularly limited, and various shapes can be mentioned. The line width can also be adjusted as appropriate depending on the mask size.
For the exposure, for example, an exposure apparatus such as a mask aligner or a stepper is used. By using these, it is possible to uniformly irradiate the entire exposed portion with parallel light rays and to accurately align the mask and the substrate. The type of the light source is not particularly limited as long as the positive photosensitive composition can be solubilized, but usually ultraviolet rays such as g-line, h-line or i-line are used.

Thereafter, a desired pattern shape can be obtained by bringing the coating film into contact with an aqueous alkaline solution to dissolve a predetermined portion, for example, an exposed portion, and developing.
The developing method may be any of a liquid piling method, a dipping method, a spray method, and the like. Further, the substrate may be inclined at an arbitrary angle during development.

The developer used for development is usually an aqueous solution containing an alkaline compound and a surfactant. The alkaline compound may be either an inorganic or organic alkaline compound.
Specific examples of the inorganic alkaline compound include sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium silicate, potassium silicate, Examples thereof include sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium borate, potassium borate, and ammonia.
Examples of the organic alkaline compound include tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, monoisopropylamine, diisopropylamine, and ethanolamine. Is mentioned.
The density | concentration in the alkali developing solution of these inorganic and organic alkaline compounds becomes like this. Preferably it is 0.01-10 mass%, More preferably, it is 0.03-5 mass%.

The surfactant in the alkaline developer may be any of a nonionic surfactant, an anionic surfactant, or a cationic surfactant.
Nonionic surfactants include, for example, polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkyl aryl ether, other polyoxyethylene derivatives, oxyethylene / oxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene Examples include ethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester, polyoxyethylene fatty acid ester, and polyoxyethylene alkylamine.
Examples of the anionic surfactant include higher alcohol sulfates such as sodium lauryl alcohol sulfate and sodium oleyl alcohol sulfate, alkyl sulfates such as sodium lauryl sulfate and ammonium lauryl sulfate, sodium dodecylbenzenesulfonate, and dodecyl sodium sulfate. And alkyl aryl sulfonates such as sodium naphthalene sulfonate.
Examples of the cationic surfactant include amine salts or quaternary ammonium salts such as stearylamine hydrochloride and lauryltrimethylammonium chloride.
The concentration of the surfactant in the alkali developer is preferably 0.01 to 10% by mass, more preferably 0.05 to 8% by mass, and particularly preferably 0.1 to 5% by mass.

  After development, washing may be performed, and post-baking may be performed as necessary. Post bake is performed at 150-250 degreeC, for example, Preferably it is 160-220 degreeC, More preferably, it is 170-200 degreeC. The post-bake time is suitably about several minutes, for example, 1 to 3 minutes.

The coating film or pattern thus obtained is useful as, for example, a photospacer used in a liquid crystal display device, a patternable overcoat, or a color filter. Moreover, a hole can be formed by using the photomask for hole formation at the time of patterning exposure to an uncured coating film, and it is useful as an interlayer insulation film. Furthermore, a transparent film or a colored film can be formed by performing only the entire surface exposure and heat curing or heat curing without using a photomask when exposing the uncured coating film. This transparent film or colored film is useful as an overcoat. Further, it can be used for a display device such as a touch panel. Thereby, it is possible to manufacture a display device having a high-quality coating film or pattern with a high yield.
The colored curable resin composition of the present invention can be suitably used for forming a coating film or a colored pattern to be a pixel of a liquid crystal display device or an image sensor. Further, a color filter and an array substrate provided with these coating films or patterns as a part of its constituent parts, and a display device including these color filters and / or an array substrate, for example, a liquid crystal display device, an organic EL device, It can be used for a solid-state imaging device.

  Hereinafter, the present invention will be described in more detail with reference to examples. In the examples, “%” and “part” representing the content or amount used are based on mass unless otherwise specified.

[Synthesis Example 1]
A mixture of 50.8 parts of a compound represented by the following formula (3-I) [trade name: PIPE-CD; manufactured by Mitsui Chemicals, Inc.], 50.8 parts of methyl isobutyl ketone and 9.5 parts of oxalic acid, 13.8 parts of formalin (containing 37% by mass of formaldehyde) was added dropwise over 1 hour with stirring at ° C. After completion of the dropwise addition, the temperature was raised to 91 ° C. and the reaction was carried out at the same temperature for 10 hours. To the reaction mixture after the reaction, 125 parts of ion exchange water and 76 parts of methyl isobutyl ketone were added and washed. Further, 51 parts of methyl isobutyl ketone and 125 parts of ion-exchanged water were added for washing, followed by dehydration by distillation, and 145.5 parts of a methyl isobutyl ketone solution (solid content: 37%) of a binder resin (resin BB). Got. The obtained binder resin (resin BB) had a weight average molecular weight (GPC, in terms of polystyrene) of 7.0 × 10 ³ .

[Synthesis Example 2]
A mixture of 50.8 parts of a compound represented by the following formula (3-I) [trade name: PIPE-CD; manufactured by Mitsui Chemicals, Inc.], 50.8 parts of methyl isobutyl ketone and 9.5 parts of oxalic acid, 13.8 parts of formalin (containing 37% by mass of formaldehyde) was added dropwise over 1 hour with stirring at ° C. After completion of the dropwise addition, the temperature was raised to 91 ° C. and the reaction was carried out at the same temperature for 10 hours. To the reaction mixture after the reaction, 125 parts of ion exchange water and 76 parts of methyl isobutyl ketone were added and washed. Furthermore, 51 parts of methyl isobutyl ketone and 125 parts of ion-exchanged water were added for washing, followed by dehydration by distillation to obtain 145.5 parts of a resin methyl isobutyl ketone solution. To the obtained resin solution, 133 parts of methyl isobutyl ketone and 363 parts of n-heptane were added and fractionated, and a binder resin (resin Bc) was taken out as a resin layer (liquid). To this binder resin (resin B-c), 145.8 parts of ethyl lactate was added to obtain an ethyl lactate solution (solid content: 33%) of the binder resin (resin B-c). The binder resin (resin B-c) obtained had a weight average molecular weight (GPC, in terms of polystyrene) of 1.3 × 10 ⁴ .

[Synthesis Example 3]
In a three-necked flask with an internal volume of 3000 ml, 17.6 parts of m-cresol, 17.6 parts of p-cresol, 15.9 parts of 2,5-xylenol, 47.6 parts of methyl isobutyl ketone, 9.7 parts of 10% aqueous oxalic acid Then, 10.0 parts of acetic acid was charged, and 27.0 parts of a 37.0% formalin aqueous solution was added dropwise over 40 minutes while stirring and heating in an oil bath at 100 ° C. Thereafter, the reaction was further continued for 15 hours. After the reaction, it was washed with water and dehydrated to obtain 103.6 parts of a methyl isobutyl ketone solution (solid content: 50%) of a binder resin (resin Bd). The obtained binder resin (resin Bd) had a weight average molecular weight (GPC, in terms of polystyrene) of 4.3 × 10 ³ .

About the measurement of the polystyrene conversion weight average molecular weight (Mw) of said resin Bb, Bc, Bd, it carried out on condition of the following using GPC method.
Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG4000HXL + TSK-GELG2000HXL (series connection)
Column temperature: 40 ° C
Solvent: THF
Flow rate: 1.0 mL / min
Injection volume: 50 μL
Detector; RI
Measurement sample concentration: 0.6% by mass (solvent: THF)
Standard material for calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500, A-500 (manufactured by Tosoh Corporation)

[Example 1]
(A) Colorant: 21 parts of a colorant represented by the formula (AI) (hereinafter referred to as “colorant Aa”),
(A) Colorant: C.I. I. 20 parts of Solvent Orange 56,
(A) Colorant: C.I. I. 18 parts of Solvent Yellow 162,
(B) Binder resin: 2 parts of resin Ba (2 parts in terms of solid content),
* Resin Ba; Marcalinker CST-15 [manufactured by Maruzen Petrochemical Co., Ltd.] (Styrene and hydroxystyrene copolymer. The proportion of hydroxystyrene is 15 mol% with respect to all copolymer units, and the weight average molecular weight. 9.0 × 10 ³ (catalog value))
(C) Photosensitizer: esterified product of o-naphthoquinonediazide-5-sulfonic acid and a compound represented by the following formula (CI) (hereinafter referred to as “photosensitive agent Ca”) 24 parts,
(D) Curing agent: 14 parts of hexamethoxymethylolmelamine,
(E) Solvent: 128 parts of ethyl lactate,
(E) Solvent: 150 parts of diacetone alcohol,
(E) Solvent: 150 parts of 1-methoxy-2-propanol (F) 2 parts of triphenylphosphine (2 parts with respect to 100 parts of the solid content of the colored curable resin composition),
Were mixed to obtain a colored curable resin composition 1. In addition, 50 ppm of silicone surfactant [SH8400: manufactured by Toray Dow Corning] was added to the composition.

  About the obtained colored curable resin composition 1, the evaluation was performed by the following method. The results are shown in Table 3.

<Pattern formation>
A planarizing film forming material mainly composed of polyglycidyl methacrylate resin is applied onto a silicon wafer by a spin coating method, heated at 120 ° C. for 2 minutes to remove volatile components, and a support having a thickness of 0.96 μm. Formed. On the support, the colored curable composition 1 was applied by spin coating so that the film thickness after pre-baking was 1.00 ± 0.05 μm. Subsequently, it prebaked at 100 degreeC for 1 minute, and formed the coating film. Thereafter, i-rays were irradiated using an exposure machine [NSR-1755i7A; manufactured by Nikon Corporation].
A photomask for forming a 3 μm square checkered pattern was used as the photomask.
After irradiation, the film was immersed in a developer (2.38% TMAH aqueous solution, 23 ° C.) for 1 minute for development. After development, it was washed with water and dried to obtain a red pattern. The film thickness of the obtained pattern was 0.95 μm as measured using a film thickness measuring device (Axiospeed; manufactured by Zeiss).

<Development unevenness evaluation>
The obtained pattern was observed from the upper surface of the pattern with a scanning electron microscope [S-4000; manufactured by Hitachi, Ltd.]. Those in which development unevenness did not occur were judged as good and those in which development was uneven were judged as bad. The results are shown in Table 3 with ◯ being good.

[Examples 2 to 9, Comparative Example 1]
A colored curable resin composition was prepared in the same manner as in Example 1 so as to have the composition shown in Table 1 and Table 2, and the resulting colored curable resin composition was obtained in the same manner as in Example 1. Evaluation was performed. The results are shown in Table 3.

  It was found that the coating film made of the colored curable resin composition of the present invention does not cause uneven development of the coating film. On the other hand, from the colored curable resin composition of the comparative example, it was not possible to form a coating film that did not cause uneven development.

  According to the colored curable resin composition of the present invention, a coating film that does not cause uneven development can be formed.

Claims (8)

  A colored curable resin composition containing a colorant (A), a binder resin (B), a photosensitizer (C), a curing agent (D), a solvent (E), and triphenylphosphine (F). The colored curable resin composition according to claim 1, wherein the colorant (A) is a colorant containing a compound represented by the formula (1).

In Expression ^(1), R 1 ~R ⁴ each independently represent a hydrogen atom, -R ⁶ or an aromatic hydrocarbon group having 6 to 10 carbon atoms. The hydrogen atom contained in the aromatic hydrocarbon group is a halogen atom, —R ⁶ , —OH, —OR ⁶ , —SO ₃ ^— , —SO ₃ H, SO ₃ M, —CO ₂ H, —CO ₂ R. ⁶ , may be substituted with —SO ₃ R ⁶ , —SO ₂ NHR ⁸ or —SO ₂ NR ⁸ R ⁹ .
R ⁵ represents —SO ₃ ^— , —SO ₃ H, SO ₃ M, —CO ₂ H, —CO ₂ R ⁶ , —SO ₃ R ⁶ , —SO ₂ NHR ⁸ or —SO ₂ NR ⁸ R ⁹ . .
m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ⁵ may be the same or different.
X represents a halogen atom.
a represents an integer of 0 or 1.
R ⁶ represents a saturated hydrocarbon group having 1 to 10 carbon atoms. A hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom. The methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom, a carbonyl group or —NR ⁷ —.
R ⁷ represents a C 1-10 saturated hydrocarbon group. A hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom. The methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or a carbonyl group.
R ⁸ and R ⁹ each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q. Alternatively, R ⁸ and R ⁹ may be bonded to each other to form a heterocyclic ring having 1 to 10 carbon atoms.
Q represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms, and a hydrogen atom contained in the aromatic hydrocarbon group and the aromatic heterocyclic group is —OH , —R ⁶ , —OR ⁶ , —NO ₂ , —CH═CH ₂ , —CH═CHR ⁶ or a halogen atom.
The hydrogen atom contained in the linear or branched alkyl group having 1 to 10 carbon atoms and the cycloalkyl group having 3 to 30 carbon atoms is a hydroxyl group, a halogen atom, -Q, -CH = CH ₂ or -CH = CHR ⁶ . May be substituted. The methylene group contained in the linear or branched alkyl group having 1 to 10 carbon atoms and the cycloalkyl group having 3 to 30 carbon atoms may be substituted with an oxygen atom, a carbonyl group or —NR ⁶ —. The hydrogen atom contained in the heterocyclic ring having 1 to 10 carbon atoms may be substituted with —R ⁶ , —OH or —Q.
M represents a sodium atom or a potassium atom. ]   The colored curable resin composition according to claim 1 or 2, wherein the content of triphenylphosphine (F) is 2 to 7 mass% with respect to the solid content of the colored curable resin composition.   The colored curable resin composition according to any one of claims 1 to 3, wherein the solvent (E) is a solvent comprising at least two solvents selected from the group consisting of ethyl lactate, propylene glycol monomethyl ether and diacetone alcohol. object.   The colored curable resin composition according to any one of claims 1 to 4, wherein the photosensitive agent (C) is naphthoquinone diazide sulfonic acid ester. The colored curable resin composition according to any one of claims 1 to 5, wherein the curing agent (D) is a curing agent having two or more divalent groups represented by the formula (2).

Wherein (2), ^{Y 1} represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ]   The coating film formed using the colored curable resin composition in any one of Claims 1-6.   The color filter formed using the colored curable resin composition in any one of Claims 1-6.